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High-Efficiency Large-Bandgap Material for Polymer Solar Cells
(2015-01-01)
Wei, Hedi
;
Chao, Yi-Hsiang
;
Kang, Chong
;
Li, Cuihong
;
Lu, Heng
High-molecular-weight conjugated polymer HD-PDFC-DTBT with N-(2-hexyldecyl)-3,6-difluorocarbazole as the donor unit, 5,6-bis(octyloxy)benzothiadiazole as the acceptor unit, and thiophene as the spacer is synthesized by Suzuki polycondensation. HD-PDFC-DTBT shows a large bandgap of 1.96 eV and a high hole mobility of 0.16 cm(2) V-1 s(-1). HD-PDFC-DTBT:PC71BM-based inverted polymer solar cells (PSCs) give a power conversion efficiency (PCE) of 7.39% with a V-oc of 0.93 V, a J(sc) of 14.11 mA cm(-2), and an FF of 0.56.
Compact Bis-Adduct Fullerenes and Additive-Assisted Morphological Optimization for Efficient Organic Photovoltaics
(2014-11-26)
Lai, Yun-Yu
;
Liao, Ming-Hung
;
Chen, Yen-Ting
;
Cao, Fong-Yi
;
Hsu, Chain-Shu
Bis-adduct fullerenes surrounded by two insulating addends sterically attenuate intermolecular interaction and cause inferior electron transportation. In this research, we have designed and synthesized a new class of bis-adduct fullerene materials, methylphenylmethano-C-60 bis-adduct (MPC(60)BA), methylthienylmethano-C-60 bis-adduct (MTC(60)BA), methylphenylmethano-C-70 bis-adduct (MPC(70)BA), and methylthienylmethano-C-70 bis-adduct (MTC(70)BA), functionalized with two compact phenylmethylmethano and thienylmethylmethano addends via cyclopropyl linkages. These materials with much higher-lying lowest unoccupied molecular orbital (LUMO) energy levels successfully enhanced the V-oc values of the P3HT-based solar cell devices. The compact phenylmethylmethano and thienylmethylmethano addends to promote fullerene intermolecular interactions result in aggregation-induced phase separation as observed by the atomic force microscopy (AFM) and transmission electron microscopy (TEM) images of the poly(3-hexylthiophene-2,5-diyl) (P3HT)/bis-adduct fullerene thin films. The device based on the P3HT/MTC(60)BA blend yielded a V-oc of 0.72 V, a J(sc) of 5.87 mA/cm(2), and a fill factor (FF) of 65.3%, resulting in a power conversion efficiency (PCE) of 2.76%. The unfavorable morphologies can be optimized by introducing a solvent additive to fine-tune the intermolecular interactions. 1-Chloronaphthalene (CN) having better ability to dissolve the bis-adduct fullerenes can homogeneously disperse the fullerene materials into the P3HT matrix. Consequently, the aggregated fullerene domains can be alleviated to reach a favorable morphology. With the assistance of CN additive, the P3HT/MTC(60)BA-based device exhibited enhanced characteristics (a V-oc of 0.78 V, a J(sc) of 9.04 mA/cm(2), and an FF of 69.8%), yielding a much higher PCE of 4.92%. More importantly, the additive-assisted morphological optimization is consistently effective to all four compact bis-adduct fullerenes regardless of the methylphenylmethano or methylthienylmethano scaffolds as well as C-60 or C-70 core structures. Through the extrinsic additive treatment, these bis-adduct fullerene materials with compact architectures show promise for high-performance polymer solar cells.
Morphological Stabilization by Supramolecular Perfl uorophenyl-C-60 Interactions Leading to Effi cient and Thermally Stable Organic Photovoltaics
(2014-03-01)
Liao, Ming-Hung
;
Tsai, Che-En
;
Lai, Yu-Ying
;
Cao, Fong-Yi
;
Wu, Jhong-Sian
A new PC61BM-based fullerene, [6,6]-phenyl-C-61 butyric acid pentafluorophenyl ester (PC61BPF) is designed and synthesized. This new n-type material can replace PC61BM to form a P3HT:PC61BPF binary blend or serve as an additive to form a P3HT:PC61BM:PC61BPF ternary blend. Supramolecular attraction between the pentafluorophenyl group of PC61BPF and the C-60 cores of PC61BPF/PC61BM can effectively suppress the PC61BPF/PC61BM materials from severe aggregation. By doping only 8.3 wt% PC61BPF, device PC(61)BP(F)651 exhibits a PCE of 3.88% and decreases slightly to 3.68% after heating for 25 h, preserving 95% of its original value. When PC61BP with non-fluorinated phenyl group is used to substitute PC61BPF, the stabilizing ability disappears completely. The efficiencies of PC(61)BP651 and PC(61)BP321 devices significantly decay to 0.44% and 0.11%, respectively, after 25 h isothermal heating. Most significantly, this strategy is demonstrated to be effective for a blend system incorporating a low band-gap polymer. By adding only 10 wt% PC61BPF, the PDTBCDTB:PC71BM-based device exhibits thermally stable morphology and device characteristics. These findings demonstrate that smart utilization of supramolecular interactions is an effective and practical strategy to control morphological evolution.
Synthesis of a New Ladder-Type Benzodi(cyclopentadithiophene) Arene with Forced Planarization Leading to an Enhanced Efficiency of Organic Photovoltaics
(2012-10-23)
Chen, Yung-Lung
;
Chang, Chih-Yu
;
Cheng, Yen-Ju
;
Hsu, Chain-Shu
;
應用化學系
We have developed a new heptacyclic benzodi(cyclopentadithiophene) (BDCPDT) unit, where 3,7-positions of the central benzo[1,2-b:4,5-b']dithiophenes (BDT) subunit are covalently rigidified with 3-positons of the two external thiophenes by two carbon bridges, forming two external CPDT rings that share two thiophene rings with the central BDT core. The distannyl-BDCPDT building block was copolymerized with 1,3-dibromo-thieno[3,4-c]pyrrole-4,6-dione (TPD) by Stille polymerization to afford a new alternating donor-acceptor copolymer PBDCPDT-TPD. The implementation of forced planarization greatly suppresses the interannular twisting to extend the effective conjugated length and preserve the interactions between the donor and acceptor segments. The device using the PBDCPDT-TPD/PC71BM (1:3 in wt%) blend processed with dimethyl sulfoxide as an additive delivered a marked PCE of 6.6% which represents a significant enhancement compared to the device using the corresponding nonfused polymer analogue with a PCE of 0.2%.
A Supramolecular "Double-Cable" Structure with a 129(44) Helix in a Columnar Porphyrin-C-60 Dyad and its Application in Polymer Solar Cells
(2012-11-01)
Wang, Chien-Lung
;
Zhang, Wen-Bin
;
Sun, Hao-Jan
;
Van Horn, Ryan M.
;
Kulkarni, Rahul R.
A novel porphyrin-C-60 dyad (PCD1) is designed and synthesized to investigate and manipulate the supramolecular structure where geometrically isotropic [such as [60]fullerene (C-60)] and anisotropic [such as porphyrin (Por)] units coexist. It is observed that PCD1 possesses an enantiomeric phase behavior. The melting temperature of the stable PCD1 thermotropic phase is 160 degrees C with a latent heat (Delta H) of 18.5 kJ mol(-1). The phase formation is majorly driven by the cooperative intermolecular PorPor and C60C60 interactions. Structural analysis reveals that this stable phase possesses a supramolecular double-cable structure with one p-type Por core columnar channel and three helical n-type C-60 peripheral channels. These double-cable columns further pack into a hexagonal lattice with a = b = 4.65 nm, c = 41.3 nm, alpha = beta = 90 degrees and gamma = 120 degrees. The column repeat unit is determined to possess a 129(44) helix. With both donor (D; Pro) and acceptor (A; C-60) units having their own connecting channels as well as the large D/A interface within the supramoleculassr double-cable structure, PCD1 has photogenerated carriers with longer lifetimes compared to the conventional electron acceptor [6,6]-phenyl-C-61-butyric acid methyl ester. A phase-separated columnar morphology is observed in a bulk-heterojunction (BHJ) material made by the physical blend of a low band-gap conjugated polymer, [poly[2,6-(4,4-bis-(2-ethylhexyl)-4H-cyclopenta [2,1-b;3,4-b']-dithiophene)-alt-4,7-(2,1,3-benzothia-diazole)] (PCPDTBT), and PCD1. With a specific phase structure in the solid state and in the blend, PCD1 is shown to be a promising candidate as a new electron acceptor in high performance BHJ polymer solar cells.
Plasmonic-enhanced performance for polymer solar cells prepared with inverted structures
(2012-11-05)
Kao, Chuan-Sheng
;
Chen, Fang-Chung
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Liao, Ching-Wen
;
Huang, Michael H.
;
Hsu, Chain-Shu
We incorporated gold nanoparticles (Au NPs) in inverted organic photovoltaic devices to enhance the device performance. The photocurrent and fill factors were improved after the addition of Au NPs into the Cs2CO3 buffer layer. The photoluminescent measurements revealed a significant increase of light absorption of the photoactive layer. We attribute the improvement to local field enhancement induced by the localized surface plasmon resonance. Further, through the study of the morphologies of the cathode interfaces, we found that the rough surfaces might increase the device resistances. This drawback, however, was overwhelmed by the advantageous plasmonic effects. (C) 2012 American Institute of Physics. [http://dx.doi.org/10.1063/1.4766736]
Porphyrin-diindenothieno[2,3-b]thiophene alternating copolymerua blue-light harvester in ternary-blend polymer solar cells
(2012-12-15)
Wu, Yu-Chun
;
Chao, Yi-Hsiang
;
Wang, Chien-Lung
;
Wu, Chun-Ta
;
Hsu, Chain-Shu
Porphyrin, despite chosen by Nature as light harvesting units, hasn't revealed its full potentials as a structural unit in porphyrin-incorporated polymers (PPors). A novel PPor was synthesized to investigate the origins of the low performances of PPor-based polymer solar cells (PSCs). The polymer features broad absorption in the blue-light region, because the diindenothieno[2,3-b]thiophene (DITT) unit extended the conjugation in the polymer backbone. PPor-DITT/PC71BM based PSCs have a high Voc (0.79 V). Their low Jsc and fill factor (FF) were attributed to the un-optimized morphology, as indicated by the photoluminescence quenching and atomic force microscopy (AFM) experiments. Using PPor-DITT as a blue-light harvesting dopant in an amorphous host leverage the strong 400550 nm absorption of PPor-DITT and circumvent the difficulties in reaching optimized morphology in the PPor/PCBM thin films. An addition of 2 wt % of PPor-DITT in ternary-blend PSCs resulted in a 10 % increase of external quantum efficiency (EQE) in the blue-light region. However, in a crystalline host, the dopant decreased the crystallinity of the host and led to large drops in FF and power conversion efficiencies (PCEs). The study provides an alternative route and expands the application of PPors in PSCs as a blue-light harvester in ternary-blend PSCs using amorphous polymers as host. (C) 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012
A Pentacyclic Nitrogen-Bridged Thienyl-Phenylene-Thienyl Arene for Donor-Acceptor Copolymers: Synthesis, Characterization, and Applications in Field-Effect Transistors and Polymer Solar Cells
(2012-09-01)
Tseng, Cheng-An
;
Wu, Jhong-Sian
;
Lin, Tai-Yen
;
Kao, Wei-Shun
;
Wu, Cheng-En
A pentacyclic benzodipyrrolothiophene (BDPT) unit, in which two outer thiophene rings are covalently fastened with the central phenylene ring by nitrogen bridges, was synthesized. The two pyrrole units embedded in BDPT were constructed by using one-pot palladium-catalyzed amination. The coplanar stannylated Sn-BDPT building block was copolymerized with electron-deficient thieno[3,4-c]pyrrole-4,6-dione (TPD), benzothiadiazole (BT), and dithienyl-diketopyrrolopyrrole (DPP) acceptors by Stille polymerization. The bridging nitrogen atoms make the BDPT motif highly electron-abundant and structurally coplanar, which allows for tailoring the optical and electronic properties of the resultant polymers. Strong photoinduced charge-transfer with significant band-broadening in the solid state and relatively higher oxidation potential are characteristic of the BDPT-based polymers. Poly(benzodipyrrolothiophene-alt-benzothiadiazole) (PBDPTBT) achieved the highest field-effect hole mobility of up to 0.02 cm2?V-1?s-1. The photovoltaic device using the PBDPTBT/PC71BM blend (1:3, w/w) exhibited a Voc of 0.6 V, a Jsc of 10.34 mA?cm-2, and a FF of 50?%, leading to a decent PCE of 3.08?%. Encouragingly, the device incorporating poly(benzodipyrrolothiophene-alt-thienopyrrolodione) (PBDPTTPD)/PC71BM (1:3, w/w) composite delivered a highest PCE of 3.72?%. The enhanced performance arises from the lower-lying HOMO value of PBDPTTPD to yield a higher Voc of 0.72 V.
New Angular-Shaped and Isomerically Pure Anthradithiophene with Lateral Aliphatic Side Chains for Conjugated Polymers: Synthesis, Characterization, and Implications for Solution-Prossessed Organic Field-Effect Transistors and Photovoltaics
(2012-06-26)
Wu, Jhong-Sian
;
Lin, Chung-Te
;
Wang, Chien-Lung
;
Cheng, Yen-Ju
;
Hsu, Chain-Shu
An isomerically pure anti-anthradithiophene (aADT) arranged in an angular shape is developed. Formation of the framework of aADT incorporating four lateral alkyl substituents was accomplished by a one-pot benzannulation via multiple Suzuki coupling. This newly designed 2,8-stannylated aADT monomer was copolymerized with a ditheniodiketopyrrolopyrrole (DPP) unit and a bithiophene unit, respectively, to furnish an alternating donor-acceptor copolymer poly(anthradithiophene-alt-dithienyldiketopyrrolopyrrole) (PaADTDPP) and a thiophene-rich poly(anthradithiophene-alt-bithiophene) (PaADTT). PaADTT with crystalline nature achieved a high FET mobility of 7.9 x 10(-2) cm(-2) V-1 s(-1) with an on-off ratio of 1.1 x 10(7). The photovoltaic device based on the PaADTDPP:PC71BM (1:2.5, w/w) blend exhibited a V-oc, of 0.66 V, a J(sc) of 9.49 mA/cm(2), and a FF of 58.4%, delivering a power conversion efficiency (PCE) of 3.66%. By adding 1.5 vol % 1-chloronaphthalene (CN) as a processing additive, the PCE can be improved to 4.24%. We demonstrated that these angular-shaped and alkylated aADT-based polymers have better organic photovoltaic (OPVs) and field-effect transistor (FETs) characteristics than the linear-shaped ADT-containing polymers.
Dithienocyclopentathieno[3,2-b]thiophene Hexacyclic Arene for Solution-Processed Organic Field-Effect Transistors and Photovoltaic Applications
(2012-04-01)
Cheng, Yen-Ju
;
Chen, Chiu-Hsiang
;
Lin, Tai-Yen
;
Hsu, Chain-Shu
;
應用化學系
We have developed a ladder-type dithienocyclopentathieno[3,2-b]thiophene (DTCTT) hexacyclic unit in which the central thieno[3,2-b]thiophene ring was covalently fastened to two adjacent thiophene rings through carbon bridges, thereby forming two connected cyclopentadithiophene (CPDT) units in a hexacyclic coplanar structure. This stannylated Sn-DTCTT building block was copolymerized with three electron-deficient acceptors, dibromo-thieno[3,4-c]pyrrole-4,6-dione (TPD), dibromo-benzothiadiazole (BT), and dibromo-phenanthrenequinoxaline (PQX), by Stille polymerization, thereby furnishing a new class of alternating donoracceptor copolymers: PDTCTTTPD, PDTCTTBT, and PDTCTTPQX, respectively. Field-effect transistors based on PDTCTTPQX and PDTCTTBT yielded high hole mobilities of 0.017 and 0.053 cm2?V-1?s-1, respectively, which are among the highest performances among amorphous donoracceptor copolymers. A bulk heterojunction solar cell that incorporated PDTCTTTPD with the lower-lying HOMO energy level delivered a higher Voc value of 0.72 V and a power conversion efficiency (PCE) value of 2.59?%.

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